2-(5-Acetyloxy-4-methyl-8-methylidene-7-oxocyclodec-3-en-1-yl)prop-2-enoic acid

Details

• Internal ID: 232a3f3a-c491-4a5e-a2d8-038f2aea4a73
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Germacrane sesquiterpenoids
• IUPAC Name: 2-(5-acetyloxy-4-methyl-8-methylidene-7-oxocyclodec-3-en-1-yl)prop-2-enoic acid
• SMILES (Canonical): CC1=CCC(CCC(=C)C(=O)CC1OC(=O)C)C(=C)C(=O)O
• SMILES (Isomeric): CC1=CCC(CCC(=C)C(=O)CC1OC(=O)C)C(=C)C(=O)O
• InChI: InChI=1S/C17H22O5/c1-10-5-7-14(12(3)17(20)21)8-6-11(2)16(9-15(10)19)22-13(4)18/h6,14,16H,1,3,5,7-9H2,2,4H3,(H,20,21)
• InChI Key: MVYLZGKQJCLZFA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.82
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9677	96.77%
Caco-2	-	0.5581	55.81%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8689	86.89%
OATP2B1 inhibitior	-	0.8551	85.51%
OATP1B1 inhibitior	+	0.9100	91.00%
OATP1B3 inhibitior	+	0.9275	92.75%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6515	65.15%
P-glycoprotein inhibitior	-	0.8604	86.04%
P-glycoprotein substrate	-	0.8081	80.81%
CYP3A4 substrate	+	0.5360	53.60%
CYP2C9 substrate	+	0.6200	62.00%
CYP2D6 substrate	-	0.9014	90.14%
CYP3A4 inhibition	-	0.7046	70.46%
CYP2C9 inhibition	-	0.8972	89.72%
CYP2C19 inhibition	-	0.8502	85.02%
CYP2D6 inhibition	-	0.8849	88.49%
CYP1A2 inhibition	-	0.6499	64.99%
CYP2C8 inhibition	-	0.7041	70.41%
CYP inhibitory promiscuity	-	0.9469	94.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8396	83.96%
Carcinogenicity (trinary)	Non-required	0.7264	72.64%
Eye corrosion	-	0.9449	94.49%
Eye irritation	-	0.6368	63.68%
Skin irritation	-	0.5733	57.33%
Skin corrosion	-	0.9596	95.96%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5532	55.32%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.6954	69.54%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	-	0.5386	53.86%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5617	56.17%
Acute Oral Toxicity (c)	III	0.5149	51.49%
Estrogen receptor binding	-	0.5411	54.11%
Androgen receptor binding	-	0.5451	54.51%
Thyroid receptor binding	-	0.7152	71.52%
Glucocorticoid receptor binding	-	0.5070	50.70%
Aromatase binding	-	0.7254	72.54%
PPAR gamma	+	0.5575	55.75%
Honey bee toxicity	-	0.8184	81.84%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9906	99.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.94%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.46%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.34%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.18%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	85.96%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.47%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.26%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.45%	93.56%

Plants that contains it

• Haeckeria punctulata

Cross-Links

• PubChem: 162944024
• LOTUS: LTS0025197
• wikiData: Q105173445